


The Rocky Horror Sam Show

by RockSaltandCherryPie



Category: Supernatural
Genre: Crossdressing Kink, Dry Humping, Feminization, First Time, Halloween, Hurt!Sam, M/M, No Sex, Panty Kink, Porn With Plot, Sam In Panties, Teenchesters, Violence, Wincest - Freeform, comforting!dean
Language: English
Status: Completed
Published: 2014-04-11
Updated: 2014-04-11
Packaged: 2018-01-19 00:53:35
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,546
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1449271
Author URL: https://archiveofourown.org/users/RockSaltandCherryPie/pseuds/RockSaltandCherryPie
Summary: <blockquote class="userstuff">
              <p>Sam goes to a Halloween party and dresses up like Frank N. Furter but ends up looking more like a girl than anything else.</p>
            </blockquote>





	The Rocky Horror Sam Show

**Author's Note:**

> I've actually been wanting to write this fic for a while now.  
> I picture the ages around 15 & 19.  
> For the record I love John and any jerky portrayal is for the sake of the story ;)
> 
> Happy Friday!

It was Halloween, and Sam had actually been invited to a party. The school he had been attending for a few months had a drama club and when he first arrived he thought it'd be fun to join. Now it was October and he had never thought he'd have made enough friends to actually be invited to a party and _know_ like half the people going.

The theme of the party was horror flicks. He had already decided on his costume. He had been reluctant at first, when two of his girlfriends (friends that were girls... he was no Casanova) suggested he go as Dr. Frank N. Furter from _The_ _Rocky Horror Picture Show_. But they pretty much begged him because they loved the movie and they planned on being the two female characters and said the group would be more complete with a Frank N. Furter. So he watched the movie over again (the last time he saw it was on a Halloween a few years ago on some cheap motel TV) and kind of liked it more the second time.

"I have the _perfect_ garter belt you can borrow. We're pretty much the same size," his friend Melinda had commented enthusiastically. He didn't know whether to be excited or bothered by the fact that he was the same size as a (rather petite) girl.

He had gathered all of the things he needed from various friends (and, regretfully, friends' moms) over the span of a week and now it was Halloween night and he was standing in front of the mirror in the small bedroom he shared with Dean, applying dark makeup on his lids.

 

Dean had been out, doing some errands for their father, who was away god knows where tonight. Possibly an old friend's, possibly a bar off some godforsaken highway getting wasted. Most likely both.

When Dean got back from the store, he brought the groceries in the small kitchen and put the food away. He preferred staying in a house like this over the motel-of-the-week because it actually had a kitchen and a fridge and cupboards. Lately he had gotten more interested in cooking up various dishes and experimenting with flavors.

"Sam?" He called, finding the house too quiet. He got no answer.

He took a chocolate pudding cup from a box of six he just got and opened it up, grabbing a spoon from the drawer and shutting it with his hip. He licked the pudding from the flimsy covering before tossing it away. He walked around the corner and down the hall, sucking a spoonful of pudding into his mouth.

"Sammy, you here?" He asked before pushing the door to their bedroom open.

There was someone standing at their dresser, reaching over and looking intently in the mirror. She was wearing all black, a corset that sat on her hips, the strings hanging loose, and pantyhose that stretched up and around her taut thighs. They were held up by one of those sexy garter things and all she was wearing under it was a black panty.

Dean's heart stuttered for a second and he stilled.

"Yeah, I'm here, Dean. Sorry. Kinda busy."

Dean's stomach convulsed when he heard his brother's voice and he nearly spat out his pudding. He coughed on it briefly before swallowing it down. "Sammy?!"

And then Sam turned to look at him, and Dean didn't hide the immediate drop his jaw did pretty much of its own accord.

He had black— _goddamn it_ _—_ makeup all around his eyes, and was holding a brush in his hand. Sam's eyes narrowed on him but he smiled at Dean anyway.

"Yeah. Didn't recognize me, huh?" He went back to applying the stuff on his eyes.

Dean's words were caught in his throat. Something stirred in his gut as his eyes travelled down Sam's lean figure, unable to believe what he was seeing.

Dean's face felt hot. But then something inside him clicked into place again and he leaned against the doorframe, a sudden pretentious smugness taking to his expression. He took a bite of pudding.

"Sam, I know we're short on money, but this?" He sighed exaggeratedly. "Well, I can't exactly say I'm surprised. Just promise me you'll be safe. And _never_ kiss on the mouth."

Sam huffed. "Dean, it's Halloween, remember?"

Dean swallowed another bite of pudding, raising his brows. "Just never figured you as the type of girl to use that as an excuse to dress like a slut, that's all."

"Dean, cut it out," Sam said, but he was laughing a little. "I'm nervous enough as it is." He put the brush down on the dresser. "My friends asked me to be Frank N. Furter and I can't back out now."

"Tim Curry?" Dean asked incredulously. "Dude, I hate to break it to you but you do _not_ have the bod to pull off Tim Curry in that movie. You look like a chick, not a tranny."

Sam just sighed, picking up a small tube that was on the dresser and popping the cap off. He twisted it in his fingers and a bright red stick poked out. He started to lean in close to the mirror but then side-glanced at Dean.

Dean was just watching him, wide-eyed.

"Cut it out."

"What?"

"Staring."

"I can't help it, man. You look like... like..." Dean tried to get something out, _anything_ , but he didn't know what to say. He already said Sam looked like a girl. If he said it again Sam might get angry.

"Just say it. I look ridiculous, don't I?" Sam's hand and the lipstick fell against the dresser.

Dean's eyes skid away when Sam looked at him with his painted cat-like eyes and his messy, feathered brown hair.

Sam was waiting for an answer, so he said, behind a weak smirk, "I'd use a lot of words to describe the way you look right now..." but didn't finish.

Sam stared back into the mirror and picked up the lipstick again. "Could you actually help me? I can't tie the stupid—thing—" he gestured at his back.

Dean discarded his pudding on the bed, not really caring if it toppled over, and walked over until he stood behind Sam. He looked at Sam in the mirror and he heard his voice coming out of him but he still couldn't believe it was him.

"I think it's just like, it ties at the top," Sam said, his voice a little shaky.

Dean wanted to ask him where he even _got_ this stuff, but there was this huge lump in his throat as soon as he touched the silky corset and lifted it up Sam's waist. He had to hold it closed as he pulled the delicate strings, trying to figure out which way they went. His hands were shaking, uncooperative, and he didn't know why. He cleared his throat to try and get the lump out but it stayed against his will.

Sam leaned forward a little, looking in the mirror to apply the lipstick, and Dean looked down at his hips jutting out under the corset and the shadowy groove of his spine that dipped all the way into the line of the garter belt.

Dean took a double-glance at the front of his jeans which were visibly bulky there, and swallowed so hard it actually made a loud _gulping_ noise that he was certain Sam must've heard. _Shit. No._ He was probably only hard because he had thought Sammy was a girl at first. Yeah. That explains that. Stupid natural hormonal reaction.

Dean finished tying the corset up despite his stupid thick fingers. "There."

When Sam turned around, Dean barely recognized him. It was like somebody took his little brother and replaced him with a little sex vixen. Dean eyed his deep red lips as Sam smiled and said "thanks, Dean."

Sam slipped on a pair of long glittery black gloves and then sat on the edge of the bed as he strapped on some pumps.

The thing was, if you'd have told Dean that his little brother would dress in drag—lipstick and tights and heels and all—just a few short hours ago, he'd have laughed in your face and imagined teasing and making fun of his brother. But now that he was actually here, looking at him, he couldn't seem to say anything at all. He just put his hands awkwardly in his pockets and tried to conceal the ridiculous bulge in his pants. Where were all his clever jokes, all his witty remarks? Sam was dressed like a _girl_ for crying out loud.

"Aren't you gonna be cold?" Was all he said finally. Sam wasn't wearing anything, really. It was all under...stuff.

"I'm gonna wear a jacket, obviously." Sam got up and experimented with his new height, wobbling a little. There was a honk that came from outside and Sam cursed.

"She's here!" He hastily grabbed his backpack that was by the bedroom door and slung it over his shoulder. For just that split second Dean saw Sammy again. His _brother_.

He watched Sam leave and followed him to the door. Sam was awkward and unsteady on the heels which made Dean almost smile.

Sam slipped on his puffy red coat by the door and looked back at Dean. "Don't wait up, I don't know how long I'll be."

"Someone gonna give you a lift home?"

"Yeah, one of my friends will." Sam zipped up his coat.

Dean leaned against the wall with his shoulder. Sam's legs were still exposed and he couldn't help staring at them like they should be covered up. He was starting to feel like a protective father or something. You know, like those Dads that don't let their teenage daughters get piercings or wear their shorts too short or their tops too low. But he told himself Sam knew what he was doing.

"Alright. Give me a call if you need anything, okay?" Dean said as Sam opened the front door and smiled back at him.

"Okay!"

"And Sam—" Sam turned, his hand on the knob. "Don't let any creepy older men hit on you, okay? They don't always have the best intentions." He was only half-joking, but Sam snickered.

And then the door slammed shut and reverberated through the empty house.

Dean let out a long breath and scratched the back of his head, looking down at his pants and rolling his eyes.

 

xxx

 

Dean spent the night at a local bar called Moe's. The female bartenders were dressed up in little frilly costumes that Dean recognized as fairytale characters. Little Red Riding Hood came and asked him what he was drinking tonight. Since he still had to drive back, he had only intended on a few beers. Just something to fog up his cluttered mind.

Dean remembered the days when he and Sam used to go trick or treating in whatever town they were staying in at the time. It was always fun.

There was a year, a long time ago, maybe six or so years, where Sam was Batman and Dean was Superman. They had collectively gotten a lot of candy.

They were walking back to Uncle Bobby's along a dirt road, passing dozens of architectural disasters, when a group of boys around Dean's age—maybe a little older—approached them out of nowhere. There were four of them, and they had pushed Sammy and knocked him on the ground, demanding his candy.

"Hey!" Dean had said, going and pushing one of them back even though he was smaller.

"What are you gonna do, _Superman_?" One of them spat. He shoved Dean so hard he almost toppled over, too. Dean looked back at Sammy, at his big puppy-dog eyes that were filled with worry, and he sighed.

"Here, just take mine and get out of here." He knew Sam wouldn't want him to get into a fight over this.

They snatched the bag, darting away laughing and satisfied with themselves and their pitiful lives.

Dean helped Sammy to his feet and inspected his scraped up elbow. "Sammy, you okay? Those stupid jerks—"

"M'fine, Dean. You didn't have to give them your candy. I was okay with giving mine."

"No chance, Sammy." Dean supported Sam the whole way back, and when they reached Bobby's Sam dumped the bag out on the carpet and said "here, we'll share" with a dewy-eyed smile.

Dean smirked at the bar, finding the contrast between Sam's costumes then and now all too amusing. Little Red asked him what brought him here all alone on Halloween night. He really didn't know how to answer that so he made up some false story about how he caught his girlfriend cheating on him with a man in a werewolf costume. She sympathized and the next beer was on the house.

 

xxx

 

The party turned out to be one of the funnest nights of Sam's teenage years so far. Since he knew everybody there nobody had made any smart remarks or offensive comments regarding his costume as he had feared. Actually everyone seemed to love it and even complimented him. He felt good.

 

The party died down at around one in the morning. Sam had secured a lift with Melinda. She was in a grade older and had borrowed her Dad's car for the night. She was only ready to leave at around two. Sam had taken off his shoes to relieve his aching feet halfway through the night and now he sat barefoot in her car as they drove.

Everyone had been drinking there but Sam only had one or two beers. He wasn't a big drinker, especially since they were all still underage. But he still felt a drowsiness taking to the lids of his eyes as he listened to the hum of the engine.

"See you later, Sam!" Melinda said once they had pulled up in front of the house and he was out of the car.

"Later!"

Sam smiled the whole way up the front drive, carrying his shoes in one hand. When he got in, the house was dark and silent. If Dean was here he might have been asleep already. Sam tossed the shoes on the entrance mat and took off his coat and hung it up.

He languorously walked inside, only when he reached the hallway he saw a dark figure looming against the wall, tall and broad. He gasped, panicking momentarily. The figure emerged, light from outside coming in through the windows to hit his rugged features. It was Dad. He took several heavy steps toward Sam and narrowed his eyes on him.

"Do you have any idea how late it is, boy?" His voice slurred as he hissed out his words, and Sam could smell the scent of liquor strong on his breath.

"I'm sorry, I was—" Sam breathed out, almost stuttering.

John's eyes flashed with something dark, then he reached out and grabbed hold of Sam's wrist, pulling him in to the light that came in through the window.

"What is this..." He inspected him, eyes traveling all the way down his body, taking in the skimpy lascivious garments. He jabbed at Sam's chest. "The fuck are you wearing? Huh?"

Sam's head thumped against the wall, and he nearly toppled over from the collision. He steadied himself, trying to speak, trying to explain. But the words were caught in his throat. So instead, he attempted to scramble away, but John grabbed a hold of his wrist again.

"It's just—it's just a costume—I was at a party—"

John slammed his shoulder into the wall with a firm palm. Sam let out an involuntary gasp.

"You look like a whore, Sam. A fucking filthy whore. You know that?"

"Dad, you're drunk..." Sam tried to reason. He and John got into fights all the time, but he had never seen him this bad before; getting more physical than verbal and spitting out crude nonsense when Sam clearly wasn't fighting back.

"Yeah, 'm drunk. But even if I was sober, Sammy," (and now he mocked a grin sloppily, his eyes taking way too long to blink) "...you'd still look like a dirty slut."

Sam's brows furrowed as he looked up at John, a deep crimson taking to his cheeks and exposed collarbone. In a sudden burst of aggression, Sam knocked John's hand away and shoved at his chest. John actually stumbled back, but Sam wasn't sure if it was because of his strength or his father's muddled brain.

John came back at him almost immediately, and Sam felt his hand collide hard with his cheek. Sam flew to the floor, his head slamming against the carpet. He felt his teeth smack against each other as his jaw clamped shut. His cheek stung and throbbed and he clutched it, scrambling to get up.

"Hey, hey!" It was Dean's voice, stern and abating the darkness. Dean crouched beside Sam, half shielding him from John and half attempting to help him gather himself.

"Did you know about this?!" John boomed, gesturing at Sam like he was something that he just scraped off the bottom of his shoe.

"It's just a costume, Dad... It's Halloween. He was at a party with some friends," Dean started to change his tone to something a little calmer, in hopes of easing John's drunken aggression.

Dean helped Sam to his feet and together they walked to the end of the hall. Dean glared over his shoulder at John even as John called out "don't walk away from me!"

Dean shut the door once they were safely in their bedroom, grateful for the little lock imbedded in the handle. Dad rarely got abusive like this. It usually meant something was troubling him and he was taking it out on whoever was accessible.

Sam was already sitting on the edge of the bed, desperately clawing at his back, trying to get out of the confines of the corset.

"Sammy..."

"This was such a stupid idea. I can't believe I even—" he gave up with the strings that he couldn't reach and fumbled with one of the little clips that held his stockings up. He violently tore the sheer nylon down his leg and discarded it on the floor.

Dean sat on the bed next to him, trying to glimpse Sammy's face which was covered by brown clumps of hair. He could hear the unsteadiness in his little brother's voice behind the apparent bravado.

"Dad was right. I look so stupid." Sam yanked his long black gloves off and tossed them on the nightstand. His hands were shaking as he went for the other leg. Dean stilled them by holding his own over them.

"Sammy."

Sam stopped, finally looking over at Dean. His eyes were red, his cheeks stained with a few stray tears, watery black leaking down right at the apples. High up on the bone, right under his eye, was a dark red spot where he had been hit. It looked like it stung. He sniffed and sloppily tried to wipe his damp cheeks dry.

Dean instinctively reached over and touched his thumb to Sam's wet cheek, wiping it. His soft skin was so warm under his fingers.

"You don't look stupid."

Sam just swallowed, letting Dean take over and he slumped forward a little, his shoulders drooping. He looked down, his black lashes fluttering and dewy. Most of the lipstick was gone now (Sam probably hadn't bothered to re-apply it during the party), and all that was left was a subtle red stain that made his lips look even poutier than they already were. Dean ran his thumb gently over the little bruise, caressing it like he wanted to make it all better.

"You look beautiful." He was barely breathing when he said it, but Sam looked up at him with his dark, wet eyes and didn't look away.

Dean's stomach stirred. He had never seen Sam look at him like this before. Maybe it was just the makeup, but he held this kind of intent darkness in his gaze, and it was stronger than ever. Dean reached over on the night stand and plucked a tissue from the little box there. "Here, hold still."

Dean swiped the tissue across Sam's cheek, then over his eye, the black gradually smearing off. Went on to the other eye, and Sam shut them pliantly, leaning in to Dean.

Dean dragged the tissue down his other cheek, then over his full red lips and Sam's eyes blinked open to look at Dean.

Dean swallowed, dragging the tissue across Sam's bottom lip which hung open a little for better access. He could feel Sam's eyes on him but he was just watching his lips, even as he stilled.

Dean really just wanted to make it all better. That was why he leaned in and planted a soft reassuring kiss on his brother's lips. Not because he looked like a work of art even all messed up like this. Not because Dean wanted to so bad he was about to jump out of his skin. And _certainly_ not because he found himself attracted to him _that_ way.

He pulled back almost immediately, searching Sam's face for any shift in his expression, but his eyes were shut, unmoving. He slowly peeled them open again, and Dean thought he should say something, try to explain.

But then Sam pressed in and kissed him back with more intent and vigor. Dean felt his stomach give a leap when Sam opened his mouth and he felt his smooth tongue inside. _What were they_ _—_ Sam's tongue pressed further in, exploring. Dean could feel a heat gathering at his groin. And Sam just kept going, insistently sucking at his bottom lip and making hot breathy noises. Dean's nerves were on fire now, and he could feel the blood eagerly gathering at his dick at a quickening pace, adrenaline kicking in.

Dean reluctantly pulled away, listening to his right mind, and held on to Sam's shoulders as he swallowed down the taste of him that was heavy in his mouth. He spun Sam around by the shoulders so that his back was to him and absently plucked at the strings of the corset to help him out of it.

They weren't supposed to be _kissing._ They were _brothers_ for crying out loud. But Sammy meant the world to him. And he really _did_ look beautiful. And Dean was fairly certain he wanted this more than anything right now. So why shouldn't they?

Sam leaned forward a little as Dean tore through the strings, yanking and pulling them out of the holes. His hands were trembling at the sight of Sammy's creamy skin, being exposed more and more as the corset began to fall apart.

He pulled the string completely out and the black corset fell loose in front of Sam.

Dean's heart nearly stopped as he took in the sight of his brother's bare back in the golden light of the room. It made his skin look like it was glowing. Dean's fingers tentatively brushed along his spine. It was just as hot as he imagined. Sam turned his head slightly, arching his back with Dean's touch.

Dean moved in, utterly transfixed, and opened his mouth on a kiss at Sam's shoulder blade. Sam turned more, following Dean's lips, and eventually their mouths found each other again.

Sam's lips were like butter, so soft, melting on his tongue. Sam turned into Dean and Dean went over him, guiding him down on his back. Sam spread his legs on either side of Dean, opening his mouth more and making little moaning noises that shot straight to Dean's cock. Dean was grateful that just moments before he had been lying in bed in just his boxers. His cock was heavy now but his boxers were airy and nonrestricting. Dean's hand travelled down Sam's bare hip to his thigh, feeling the fabric of the nylon under his fingertips. With a groan, he dipped his fingers slightly under the band, feeling the elastic give. Sam wrapped his leg around Dean more and eagerly pushed his hips up to get some contact. Dean felt Sam's dick pressing hard at the confines of the panty as they ground against each other.

They gasped and rubbed their hips around, up and down and in circles, everything making Dean's head spin. Sam held on to his shoulders and moaned, tossing his head back. Dean kissed his exposed neck and licked a stripe up his Adam's apple. He sucked at his jaw and breathed heavy in his hair. Sam squirmed and pushed up, rolling their bodies around so that he was on top of Dean, straddling his hips. Dean took in the sight of him—brown hair messy and sticking to his face, kiss-ridden lips puffy and glistening—and slid his hands up Sam's thighs. One of them was bare and the other was concealed under sheer black. He stroked the garter belt with his thumb, loving the feel of the silky fabric. Sam pushed his hips into Dean's touch, craving the contact. Dean ran his thumb along the line of Sam's cock through the black panty and Sam whimpered and pressed his palms into Dean's stomach to support his trembling body. Dean dug his thumb into the head, circling around it and finding the cotton damp. Sam gasped and jerked, then began rolling his hips around until their cocks caught and dragged easily against each other.

They moved as one, picking up the pace of their thrusts. Dean clutched on to Sam's small hips, watching the little black panty stretch and bunch under the garter belt which was now riding up on one side.

"Fuck, Sammy..."

Sam dug his fingers into Dean's stomach, heaving and gasping and desperately pushing. His eyes were still wet at the corners, remnants of black still evident underneath.

Dean was up to his breaking point already, but then Sam's little hands pushed up his shirt and explored underneath, fingers dragging against his bare flesh.

Dean's muscles clenched and he felt his balls drawing up. If Sam kept moving like that—

And then Sam was pushing his hips down as hard as he could and Dean's fingers bore in to Sam's thighs, leaving bold white imprints in his skin. The friction caused the fabric between them to heat up and all of the overstimulation brought them both over the edge. They came at the same time, and it was hot and desperate and loud. Sam whined and fell down a little as he continued to push, clutching Dean's chest and spurting in his little panties. Even through two layers of fabric Dean could feel Sam's cock convulsing with his, getting all wet and sticky.

Sam collapsed on Dean's chest, the two of them completely wrung out and boneless. Together they heaved for a good few minutes, hopelessly trying to catch their breath without much success; the air way too hot and heavy.

They stayed that way, Sam sprawled on top of Dean, Dean holding him, until their panting died down.

Dean stroked through Sammy's hair and along his arms, soothing him until they fell asleep.


End file.
